US8609755B2 - Storage stable composition of partial and/or complete condensate of hydrolyzable organofunctional silane - Google Patents
Storage stable composition of partial and/or complete condensate of hydrolyzable organofunctional silane Download PDFInfo
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- US8609755B2 US8609755B2 US11/541,333 US54133306A US8609755B2 US 8609755 B2 US8609755 B2 US 8609755B2 US 54133306 A US54133306 A US 54133306A US 8609755 B2 US8609755 B2 US 8609755B2
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- 0 C[1*]CC Chemical compound C[1*]CC 0.000 description 8
- LVACOMKKELLCHJ-UHFFFAOYSA-N [H]N(CCC[Si](OC)(OC)OC)C(N)=O Chemical compound [H]N(CCC[Si](OC)(OC)OC)C(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 description 1
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- C23C22/48—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6 not containing phosphates, hexavalent chromium compounds, fluorides or complex fluorides, molybdates, tungstates, vanadates or oxalates
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
- C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
- C23C22/06—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6
- C23C22/48—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6 not containing phosphates, hexavalent chromium compounds, fluorides or complex fluorides, molybdates, tungstates, vanadates or oxalates
- C23C22/50—Treatment of iron or alloys based thereon
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- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
- C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
- C23C22/06—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6
- C23C22/48—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6 not containing phosphates, hexavalent chromium compounds, fluorides or complex fluorides, molybdates, tungstates, vanadates or oxalates
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- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
- C23C22/73—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals characterised by the process
- C23C22/74—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals characterised by the process for obtaining burned-in conversion coatings
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- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
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- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C2222/00—Aspects relating to chemical surface treatment of metallic material by reaction of the surface with a reactive medium
- C23C2222/20—Use of solutions containing silanes
Abstract
Description
wherein each occurrence of R1 is independently a linear, branched or cyclic divalent organic group of 1 to about 12 carbon atoms, more specifically 1 to about 10 carbon atoms, and most specifically from 1 to about 8 carbon atoms, such as the non-limiting examples of methylene, ethylene, propylene, isopropylene, butylene, isobutylene, cyclohexylene, arylene or alkarylene forming a stable bridge between organofunctional group X and the silyl group, and optionally containing one or more heteroatoms, such as the non-limiting examples of O and S; each occurrence of R2 independently is alkyl, alkoxy-substituted alkyl, aryl, or aralkyl, all of specifically from 1 to about 16 carbon atoms, more specifically from 1 to about 12 carbon atoms and most specifically from 1 to about 8 carbon atoms, each R3 independently is hydrogen, acetyl, alkyl, or alkoxy-substituted alkyl, all of specifically from 1 to about 16 carbon atoms, more specifically from 1 to about 12 carbon atoms and most specifically up to about 8 carbon atoms X is an organofunctional group; of valence r, including mono-, di- or polyvalent functional groups, r is an integer of 1 to 4, and a is an integer of from 0 to 2, more specifically 0 to 1 and most specifically 0.
wherein each occurrence of R independently is hydrogen, alkyl of from 1 to 6 carbon atoms, cycloalkyl, alkenyl of from 1 to 6 carbon atoms, arylene or alkarylene, and specifically the R which is bound to the nitrogen atom that is a bridge between the carbonyl and R1, is individually selected from the group consisting of hydrogen, methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, sec-butyl, tert-butyl, and cyclohexyl; R1 is a substituted or unsubstituted aliphatic or aromatic group, specifically R1 is selected from the members of the group consisting of an alkylene of from 1 to 10 carbon atoms, alkenylene of 1 to 6 carbon atoms, arylene and alkylarylene and some non-limiting examples of R1 are methylene, ethylene, propylene, 2-methylpropylene and 2,2-dimethylbutylene; each R2 independently is a monovalent hydrocarbon group from 1 to 10 carbon atoms, more specifically 1 to about 6 carbon atoms, specifically such as the non-limiting examples of alkyl, aryl and aralkyl groups such as the non-limiting examples of methyl, ethyl, butyl, hexyl, phenyl, or benzyl, more specifically, the lower alkyls of from 1 to 4 carbon atoms and most specifically methyl; and R3 each is independently chosen from the group consisting of hydrogen, linear or branched alkyl, linear or branched alkoxy-substituted alkyl, linear or branched acyl, specifically R3 is individually chosen from the group consisting of hydrogen, ethyl, methyl, propyl, iso-propyl, butyl, iso-butyl, sec-butyl and acetyl; and in one embodiment, at least one R3 is other than hydrogen or acetyl; and a is 0, 1 or 2.
In another specific embodiment one non-limiting example of ureido silane herein can be 3-ureidopropyltriethoxysilane which can also be used to prepare the hydrolyzates, which can be used in the compositions and methods described herein. Pure 3-ureidopropyltriethoxysilane is a waxy solid material. A solvent or means of solubilizing the solid material is needed for it to be useful. In one specific embodiment herein, commercially available 3-ureidopropyltriethoxysilane is dissolved in the non-limiting example of methanol, and as a result, it is not a pure compound but contains both methoxy and ethoxy groups attached to the same silicon atom. In one embodiment commercially available 3-ureidopropyltriethoxysilane is dissolved in methanol so that methanol makes up 50 weight percent solution of the solution of ureidopropyltrialkoxysilane and methanol. In another specific embodiment herein, when fully hydrolyzed, the identity of the silanes would be identical.
wherein R7 is a monovalent hydrocarbon group having from 1 to 10 carbon atoms, more specifically from about 1 to about 8 carbon atoms and most specifically from about 1 to about 4 carbon atoms, or OR8 and each R8 is independently chosen from C1-C4-alkyl. In one even more specific embodiment herein some non-limiting examples of formula (IV) can be at present, tetraethylorthosilicate (TEOS) or methyltriethoxysilane can be mentioned. In one embodiment herein, these compounds of formula (IV) and others encompassed by the formula will hydrolyze in solution (such as aqueous solution) to provide a source of Si—O bonds. In one other embodiment herein the composition(s) and method(s) herein can further comprise water specifically in addition to any water present in aqueous cerium oxide sol described herein.
TABLE 1A | |||
Comparative Examples | Ex | Ex |
A1 | B1 | C1 | D1 | E1 | |
Aminopropyltrimethoxysilane | 5% | 5% | 5% | ||
Ureidopropyltrimethoxysilane | 5% | 5% | |||
Colloidal cerium oxide (20%) | 2% | 2% | |||
Colloidal silica (34%) | 2% | ||||
Water | 95% | 93% | 93% | 95% | 93% |
pH | 6 | 6 | 6 | 3 | 3 |
TABLE 1B |
NSS Exposure millimeters (mm) Creep |
EG | CRS | |||
Formulation | 96 Hours | 96 Hours | ||
A1 Comparative | 5 | 5 | ||
B1 Comparative | 3 | 3 | ||
C1 Comparative | 5 | 2 | ||
Ex D1 | 0.7 | 0.7 | ||
Ex E1 | 0.5 | 0.4 | ||
Control-Iron phosphate/chrome seal | 0.6 | 0.5 | ||
Control-Zinc phosphate chrome seal | 0.6 | 0.3 | ||
TABLE 2A |
Formulations |
Comparative | |||||||
Ex | Ex | Ex | Ex | Ex | Examples | Ex |
A2 | B2 | C2 | D2 | E2 | F2 | G2 | H2 | |
Wt % CeO2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
(20%) | ||||||||
Wt % | 2.5 | 2.5 | 1.3 | 1.7 | 1.9 | |||
Silquest | ||||||||
A-1524 | ||||||||
Wt % | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
Cabosperse | ||||||||
A205 | ||||||||
Silquest | 1.3 | 0.9 | 0.7 | |||||
A-1100 | ||||||||
Silquest | 2.5 | |||||||
A-1637 | ||||||||
Silquest | 2.5 | |||||||
A-1110 | ||||||||
Silquest | 2.5 | |||||||
A-186 | ||||||||
Water | 94.5 | 96.5 | 94.4 | 94.4 | 94.4 | 94.5 | 94.5 | 94.5 |
Note - | ||||||||
for samples B2 through G2, acetic acid was added to adjust the pH of the treatment solution to 4.0 to 4.3. | ||||||||
Cabosperse A205 - 12% active colloidal silica available from Cabot Corporation. | ||||||||
Silquest A-1524 - gamma-ureidopropyltrimethoxysilane available from GE Silicones. | ||||||||
Silquest A-1100 - gamma-aminopropyltriethoxysilane available from GE Silicones | ||||||||
Silquest A-186 - beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane available from GE Silicones. | ||||||||
Silquest A-1637 - delta-aminohexyltrimethoxysilane available from GE Silicones. | ||||||||
Silquest A-1110 - gamma-aminopropyltrimethoxysilane available from GE Silicones. | ||||||||
MeO(EO)7.5—CH2—CH2—CH2—Si—(OMe)3 is Silquest A-1524 wherein MeO is methoxy and (EO) is an oxyethlyene group. |
TABLE 2B |
NSS Exposure |
mm Creep |
HDG | HDG | CRS | CRS | |
Formulation | 168 Hours | 336 Hours | 168 Hours | 336 Hours |
Ex A2 | 0.8 | 2.3 | 2.1 | 5.3 |
Ex B2 | 7.4 | 10.1 | 2.2 | 6.1 |
Ex C2 | 20+ | NA | 3.85 | NA |
Ex D2 | 20+ | NA | 4.2 | NA |
Ex E2 | 20+ | NA | 4.0 | NA |
F2 Comparative | 20+ | NA | 8.5 | NA |
G2 Comparative | 20+ | NA | 20+ | NA |
Ex H2 | 20+ | NA | 20+ | NA |
NA - rating is not available. Panel had been removed from testing at earlier exposure time. |
TABLE 3 |
Stabilizing Effect of Additives |
Appearance |
Sample | % A-1524 | % CeO2 | Additive | % Additive | Initial | 21 days | 45 days | 3.4 mos. | 6.4 mos. |
A3 | 15 | 5 | None | 0 | yellow | precipitate* | |||
solution | |||||||||
B3 | 15 | 5 | EtOH | 15 | yellow | yellow | yellow | yellow | yellow |
solution | solution | solution | solution | solution | |||||
C3 | 15 | 5 | EtOH | 10 | yellow | yellow | slight haze | gel | |
solution | solution | ||||||||
D3 | 15 | 5 | EtOH | 5 | yellow | yellow | precipitate* | ||
solution | solution | ||||||||
E3 | 15 | 5 | Dowanol PM | 5 | yellow | yellow | milky | precipitate* | |
solution | solution | solution | |||||||
F3 | 15 | 5 | propylene glycol | 5 | yellow | yellow | precipitate* | ||
solution | solution | ||||||||
G3 | 15 | 5 | propylene glycol | 10 | yellow | yellow | slight haze | slight haze | translucent |
solution | solution | ||||||||
*precipitate with clear liquid on top | |||||||||
Dowanol PM is 1-methoxy-2-propanol | |||||||||
EtOH is ethanol | |||||||||
Samples A3, B3, C3, D3, E3, F3 and G3 are all examples except that A3 omits the presence of stabilizing agent. | |||||||||
CeO2 is a 20% colloidal dispersion of cerium oxide particles in water |
TABLE 4 |
Effect of Additional Stabilizing Agents |
% A-1524 | % CeO2 | Additive | % Additive | Initial | 1 day | 17 days | 50 days | 3.5 months | 6 months | |
A4 | 15 | 5 | EtOH | 5 | clear yellow | clear yellow | translucent | precipitate | ||
B4 | 15 | 5 | EtOH | 10 | clear yellow | clear yellow | translucent | translucent | translucent | opaque solution |
C4 | 15 | 5 | Acetone | 5 | clear yellow | clear yellow | translucent | translucent | opaque | milky white |
solution | ||||||||||
D4 | 15 | 5 | Methyl | 5 | clear yellow | clear yellow | translucent | precipitate | ||
acetate | ||||||||||
E4 | 15 | 5 | A-1230 | 5 | clear yellow | clear yellow | clear yellow | clear yellow | clear | clear yellow |
yellow | solution | |||||||||
F4 | 15 | 5 | Dowanol PM | 5 | clear yellow | clear yellow | translucent | translucent | precipitate | |
G4 | 15 | 5 | Dowanol PM | 10 | clear yellow | clear yellow | translucent | translucent | translucent | translucent solution |
H4 | 15 | 5 | None | 0 | clear yellow | clear yellow | precipitate | |||
I4 | 15 | 5 | A-1110 | 5 | milky white | precipitate | ||||
with clear | ||||||||||
solution | ||||||||||
J4 | 15 | 5 | A-1100 | 5 | milky white | precipitate | ||||
with milky | ||||||||||
solution | ||||||||||
K4 | 15 | 5 | A-1110 | 1.5 | milky white | white gel | ||||
L4 | 15 | 5 | A-1100 | 1.8 | milky white | white gel | ||||
A-1230 is a polyether silane available from GE Silicones | ||||||||||
A-1110 is gamma-aminopropyltrimethoxysilane available from GE Silicones | ||||||||||
A-1100 is gamma-aminopropyltriethoxysilane available from GE Silicones | ||||||||||
Dowanol PM is predominantly 1-methoxy-2-propanol available from Dow Chemical. | ||||||||||
CeO2 is a 20% colloidal dispersion of cerium oxide particles in water |
All of the examples A4, B4, C4, D4, E4, F4, G4, H4, I4, J4, K4, and L4 in table 4 are examples, except that H4, I4, J4, K4 and L4 omit stabilizing agent or use other than the herein described stabilizing agent.
TABLE 6A | |||||
6A | 6B | 6C | 6D | 6E | |
Ureidopropyltrimethoxysilane | 30% | 30% | 30% | 30% | 30% |
Colloidal cerium oxide (20%) | 10% | 10% | 10% | 10% | 10% |
2-methyl-1,3-propanediol | 10% | 5% | |||
2-methyl-2,4-pentanediol | 10% | 10% | 5% | ||
Dowanol PM | 3% | 3% | 3% | 3% | 3% |
Silquest A-1230 | 2% | ||||
Water | 47% | 47% | 52% | 45% | 52% |
TABLE 6B |
NSS Exposure CRS |
mm Creep |
CRS | |||
Formulation | 336 Hours | ||
6A | 3.20 | ||
6B | 2.50 | ||
6C | 2.80 | ||
6D | 4.40 | ||
6E | 2.20 | ||
Iron phosphate/chrome seal (Permatreat 2102/ | 7.70 | ||
Chemseal 7750) available from GEWPT | |||
Chrome No-Rinse (Permatreat 1510) available | 2.2 | ||
from GEWPT | |||
Multi Metal-Chrome No-Rinse (Permatreat 1500) | 7.9 | ||
available from GEWPT | |||
TABLE 6C |
NSS Exposure HDG |
mm Creep |
HDG | |||
Formulation | 500 Hours | ||
6A | 2.65 | ||
6B | 1.08 | ||
6C | 2.93 | ||
6D | 4.60 | ||
6E | 1.65 | ||
Zinc phosphate/chrome seal (Permatreat 2325/ | 1.4 | ||
Chemseal 7750) available from GEWPT | |||
Multi metal Chrome No-Rinse (Permatreat 1500) | 2.2 | ||
available from GEWPT | |||
TABLE 6D |
AASS Exposure Aluminum |
mm Creep |
Aluminum | |||
Formulation | 500 Hours | ||
6A | 1.25 | ||
6B | 1.58 | ||
6C | 1.25 | ||
6D | 1.15 | ||
6E | 1.25 | ||
Multi-metal Chrome No-Rinse (Permatreat 1500) | 0.03 | ||
Claims (23)
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US11/541,333 US8609755B2 (en) | 2005-04-07 | 2006-09-29 | Storage stable composition of partial and/or complete condensate of hydrolyzable organofunctional silane |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US11939490B2 (en) | 2017-07-31 | 2024-03-26 | Momentive Performance Materials Inc. | Curable surface-protective coating composition, processes for its preparation and application to a metallic substrate and resulting coated metallic substrate |
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Also Published As
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KR101510259B1 (en) | 2015-04-08 |
CA2603708C (en) | 2014-07-08 |
EP1871924A1 (en) | 2008-01-02 |
EP1871924B1 (en) | 2015-05-06 |
US20070090329A1 (en) | 2007-04-26 |
JP2008537980A (en) | 2008-10-02 |
BRPI0610448B1 (en) | 2018-02-06 |
CN101248213A (en) | 2008-08-20 |
RU2007141164A (en) | 2009-05-20 |
JP4958895B2 (en) | 2012-06-20 |
RU2410468C2 (en) | 2011-01-27 |
CA2603708A1 (en) | 2006-10-19 |
US10041176B2 (en) | 2018-08-07 |
MX2007012320A (en) | 2008-03-07 |
WO2006110328A1 (en) | 2006-10-19 |
KR20070121041A (en) | 2007-12-26 |
TW200700580A (en) | 2007-01-01 |
US20060228470A1 (en) | 2006-10-12 |
TWI395835B (en) | 2013-05-11 |
BRPI0610448A2 (en) | 2010-06-22 |
CN101248213B (en) | 2012-09-05 |
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